Job Openings

PART TIME CITATION HEARING OFFICER
 

The Town of Winchester seeks a fair, impartial, and dependable Part time (10-20 hrs.) Citation Hearing Officer to conduct administrative hearings on contested citations, including automated speed-enforcement, may at a future date include red-light, parking, municipal-code, and other civil or administrative violations assigned by law or ordinance. The Hearing Officer serves as a neutral decision-maker, independently evaluates the record and testimony, applies applicable Connecticut law and Town ordinances, and issues timely, clear decisions. This is an adjudicative role; the Hearing Officer does not issue, approve, investigate, collect, or prosecute citations.

Salary $30.00 per hour.  

 

Complete job description and application available from the office of the Town Manager, Town Hall, 338 Main Street, Winsted, CT 06098 or www.townofwinchester.org/our-town/pages/job-postings

The position applying for “Part Time Citation Hearing Officer” must be clearly marked on subject line of the email or on the front of the envelope if mailing.  Applications to be considered can be emailed to Terry Hall, thall@townofwinchester.org or mailed to Town of Winchester, 338 Main Street, Winsted, CT 06098, Attention: Terry Hall by October 30, 2026

EEO/AA/M/F/D/V

 

$26.10 - $30.77hr
 The Town of Winchester has an opening for a Highway Maintainer III at the Department of Public Works.  Complete job description and application available from the office of the Town Manager, Town Hall, 338 Main Street, Winsted, CT 06098 
 Please send resume, and completed application by email to thall@townofwinchester.org with “ Maintainer III” in the subject line or by mail to Town Manager’s Office , 338 Main Street, Winsted, CT 06098 with  “ Maintainer III” clearly marked on the front of the envelope.  EEO/AA/M/F/D/V

 

Part-Time (19 hours) Leasing & Occupancy Coordinator –Monday – Thursday 9am – 2pm. 

Performs all aspects of office processes for the Winchester Housing Authority Public Housing 

programs. 

 

 Send letter of interest with qualifications before August 28,  2026, to: Winchester Housing Authority
80 Chestnut Street 
Winsted, CT 06098 
Attention: Executive Director. 

No Phone Calls Please. EOE

 The Town of Winchester is accepting applications for entry level police officers to fill full time positions. Candidates must be 21 years of age and possess a valid Connecticut Driver License and a high school diploma or equivalent.  All candidates must pass the CPCA Written exam prior to submitting a completed application to the Town of Winchester and will be required to successfully complete written and oral examinations, physical wellness exam including drug screening, background investigation, polygraph examination, psychological examination, and Police Chief’s interview. Entry level candidates must provide proof of passing the CHIP Physical Abilities Assessment prior to the written test being given. The salary range is $55,944 to $74,362.  Deadline for application is.  To submit an application or view a more complete job announcement go to www.PoliceApp.com/WinchesterCT
The Town of Winchester is an Equal Opportunity/Affirmative Action Employer.

 

PART TIME ALTERNATE SCHOOL CROSSING GUARD

TOWN OF WINCHESTER, CT

Salary $16.35/hr.  

 

The Town of Winchester, CT is seeking candidates to be considered for part time School Crossing Guard for the Winsted Police Department.  Job description and application available from the Town Manager's office, Town Hall, 338 Main Street, Winsted, CT 06098 or at https://www.townofwinchester.org/job-openings

Completed applications can be dropped off at the Police Department, 338 Main Street, Winsted, CT 06098 open until filled.  EEO/AA/M/F/D/V